Blog Post

Curiosity Kills the Quota

I recently spoke to Robert Gillette, the host of the podcast Reclaiming Sales. It was a great conversation! We discussed many things that will benefit beginning sales professionals. Specifically, we discussed:

  1. Get to know your prospects better, understand how they make and lose money.
  2. Get curious, and stay that way… even when you’ve heard your 100th prospect tell you the same thing.
  3. Build your belief, it will keep you company when times get tough.

You can listen to our conversation by subscribing to Robert’s podcast here. You can also subscribe by going to Apple Podcasts, Google Podcasts, Spotify, and many more that are listed here.

The following is a transcription of our conversation for those that prefer to read rather than listen. The transcription is as close as possible to the spoken word but effort was made to try to make it a little more readable with fairly grammar correct phrasing, sentence structure, and paragraph structure. Where the commentary overrode grammar or the use of synonyms, the spoken word was chosen.

Announcer 0:30  

You’re listening to Reclaiming Sales because you don’t need to sell your soul to be successful with your host and fellow salesman, Robert Gillette.

Robert Gillette 0:41  

Robert Gillette
Reclaiming Sales Podcast Host

Hey everybody, welcome back to the show. My name obviously is Robert Gillette, and I have a new friend of mine. I know everybody I meet on the show, I say my new friend, but it’s true so far—a gentleman named Sean O’Shaughnessey. Honestly, the reason why you’re on the show, to be totally honest, is he, you engage with me, you commented on the things that I post, and you send me messages. And you know, when you’re doing a podcast, it’s like screaming into the void. And so when the void reaches back out and gives you feedback, it’s incredibly helpful. I’m used to performing on stage, in general, so I just wanted to have you on the show, first of all, to get your perspective on what we’ve been talking about so far. But, still, you also have some pretty deep claws into this whole sales game as well, and you have some perspectives that I just want to explore and see what we can uncover over the next 20 minutes or so. But before we get onto that, Sean, why don’t you, I guess before you take off your sales guy hat, what do you sell and who do you sell it to.

Sean O’Shaughnessey 1:42  

I am the CEO of a company called New Sales Expert. I sell sales management to companies with bad sales management or don’t know how to have sales management.

Robert Gillette 1:56  

Okay, and we don’t have a lot of, you know, people on the show who aren’t salespeople. But I guess my first question to you before we move too far into this is. Do you think it’s harder to sell to salespeople or to sell to non-salespeople? Is it hard to sell to people who sell for a living?

Sean O’Shaughnessey 2:16  

Sean O’Shaughnessey
CEO and President
New Sales Expert, LLC

So it’s I think it’s easier to sell to salespeople because we like to hear a good pitch. I actually sell, though, to the CEO that is frustrated because he doesn’t know how to manage a sales force. So that’s actually whom I sell to. And that’s the problem I solve.

Robert Gillette 2:32  

Okay, so you’re actually selling to a CEO or someone at that C suite level.

Sean O’Shaughnessey 2:37  

Correct. I’m usually selling to the founder of the company. And he is in a situation where he can’t figure out how to manage salespeople, how to recruit salespeople, and how to make salespeople better. So that’s what I do for him or her.

Robert Gillette 2:51  

Unfortunately, mostly him, but we’re working on that diversity by brute force. We’re doing it as a country anyways. 

So let’s, let’s roll this back to the beginning of your career, how did you get into sales. And why did you stick with it all those years?

Sean O’Shaughnessey 3:11  

 I’ve been in sales for 36 years. I got into sales because I was a really lousy engineer. I graduated with a mechanical engineering degree. The last day I was a mechanical engineer was when I got my degree. That is when I walked offstage, cussed out my physics professor because I couldn’t stand him, and I said, “I’m done with this.” 

I’ve been lucky as I actually had job offers when I got out of college to go into technical sales. So I was lucky I went to a really great company. I won’t state the name of the company unless you want me to, but I went to a really great company, and they put me through sales training for 11 months. So it was the best career decision I ever made in my life was to accept that job, and I was too naive at the time to realize it because I had no idea that’s what they were going to do and how great that was going to be for my career.

Robert Gillette 3:57  

So, then we get straight someone hired you to go into sales. And then for 11 months, you didn’t carry a quota, you didn’t sell anything to anybody, you just….

Sean O’Shaughnessey 4:05  

Nope. So, so back then, that was a possibility. There were a couple of companies out there that that still did it. A lot of companies used to do it back 100 years ago, but that was a relatively rare thing to have. They saw enough in me to teach me how to be a salesperson, how to be a professional salesperson. They sent me to class for 11 months, their our own class that they did. There were 15 of us that went through that class at that time. We were classmates. We essentially felt that we received an MBA in sales. It was the best, easily the best decision I’ve ever made in my career, nope, no decision made since then has been anywhere close to that, and I didn’t even know at the time. 

Robert Gillette 4:47  

Okay, so help me understand, what did you do for 11 months? What did you study? 

Sean O’Shaughnessey 4:51  

I studied how to do a product demonstration how to explain products to the customer. I had to learn every single product that that company made, and they made a lot of products. I had to understand how to do a presentation in front of 100 people. Their products were sold through distribution, and they would bring their distributors back into the corporate headquarters, and they would teach them, especially the new people. Those new people were taught by us. Those people were going through product sales training. So, about seven or eight weeks of that 11 months, we literally were explaining a product to a different group every week. And that would take a week of prep, on how we were going to explain this brand new product as we had never reused a product in our training, we’d have to explain a brand new product to this group of 100 people that were desperate to learn how to sell the product. We were the experts for that week. That was amazingly good preparation on how to talk; how to speak in front of a group. 

And then, we went through in-depth knowledge and in-depth conversations on how to negotiate a deal; how to set up a sales call at the beginning of a sales call; how to close a sales call. We had people brought in to teach us negotiation. We had people brought in to teach us how to dress. Finally, after everything they taught us, we were ready to fight bear when they got done. 

Robert Gillette 6:11  

And how long did you end up staying at that company? 

Sean O’Shaughnessey 6:13  

Four years. A bad investment on their part. 

Robert Gillette 6:18  

Was that pretty common? I mean, how long do you think they expected you to stay 

Sean O’Shaughnessey 6:22  

They actually expected us to stay for five or six years probably. But, amazingly, and I just ran into a classmate. He was in my class and started the same day I did. He is currently the chairman and CEO of that company he never left. He stayed there the entire time, got promoted 50 times in his career, and now sits on top of what is now probably a four-and-a-half billion-dollar company. So, he probably did better than I did because he stuck it out. He became successful by doing that. I just went on kept selling for other people. 

Robert Gillette 6:52  

That’s interesting. There’s always that tension between do I stay or do I go, you know, as we’re growing because if you had stayed, one of you wouldn’t have gotten that job.

Sean O’Shaughnessey 7:03  

So, it’s interesting because that’s a lot like the conversations that I have with salespeople now, “Don’t give up!” In essence, I gave up, and he didn’t. He arguably has a better career outcome than I did, but he didn’t give up. He stayed. He stuck it out. I didn’t do that.

Robert Gillette 7:21  

let’s explore that for a minute; why did you give up? I mean, they gave you all this training. If you’ve been there for four years, then you succeeded for at least two of those. Why did you leave after your third year of boots on the ground?

Sean O’Shaughnessey 7:35  

The company was an old-style company. Once again, I won’t give the name of the company, but it was an old-style company. They would say, “You haven’t been here for ten years, so no, you don’t get that account yet.” This is probably very similar to many of your listeners, where you see somebody else in the office, and they got all the great accounts; they have all the cushy accounts. My solution to that problem was to give up to go somewhere else that would appreciate what I did. His solution was to keep fighting it out, and you know, maybe be successful. So, once again, we would argue as to who had a better career after that. But, don’t give up because that’s a really, really critical thing in sales. As soon as you feel like you can’t take it any longer, that’s when holding on a little bit longer actually hits, and that great thing will happen. I don’t know if you’re a water skier, but they’ll tell you when you learn how to water ski, “The minute that you think you’re going to let go all the rope, that’s when you shouldn’t let go of the rope. That’s when you’re going to stand up and get up the first time.”

Robert Gillette 8:35  

That’s why I don’t water ski, but I appreciate the analogy. I’m going to be a millennial now. I’m sorry, but that was then, and this is now. Obviously, that was a company that understood the value of investing in their salespeople and their staff for the long term. If you’re going to invest in people like that, they’re going to reward longevity. Do you think it makes sense in today’s sales environment? Where people aren’t going to train you just enough that you don’t fall flat on your face right out of the gate, and it’s kind of up to you to be the “salesperson extraordinaire” in the future. Does it make sense to still stick with a company, even when it’s hard, or you’re not making money, or this the territory deck is stacked against you? 

Sean O’Shaughnessey 9:24  

It probably does make sense, although I never followed that sound wisdom in my career. I’ve probably changed jobs 15 times in my 36 years of sales and sales management. So, I have never subscribed to the last up. I’ve always felt that there’s greener grass somewhere else. So maybe I’m not the best person to ask for that advice. I will tell people how to be successful. I don’t think that in today’s economy, it makes sense for a company to invest that much in a salesperson. That was a considerable expense. Investing 11 months though the pay scale is different from today’s, it’s still massive for a percentage of what I was making. That was just a large number of dollars that they spent on me. I don’t know that they got their investment out of it. I don’t know. They don’t do it anymore. So they probably don’t think that it’s a good investment.

Robert Gillette 10:17  

So when you’re looking at a company, and they just hired you. They sign the contract, and it’s your first day on the job. Where do you look first? Where do you start making changes right out of the gate?

Sean O’Shaughnessey 10:29  

The very first thing that I do is I go to the salespeople that are there. I say, “imagine that you have my job; what would you do?” Invariably, the salespeople that are there. They are struggling with things. They’re struggling with things inside of their control or struggling with things outside of their control. The first thing I do as a sales manager is to figure out which things are outside of their control. But I also want to know a little bit of what they can control, and a lot of that is a little bit of self-discipline. They can do better. I realize everybody tries really hard to be self-disciplined, but I give them suggestions on how to be successful, how to learn, how to ask questions of customers. 

I become the salesperson’s best advocate because the CEO just hired me to come in and fix the sales organization. I turn around a week and a half later and say, “Okay, I’ve met with all your salespeople, these are the things that you have to fix in the company, and the salespeople can’t touch.” And that’s just a reality of life, but salespeople are often stuck in a situation they can’t get the things they need and can’t get the support they need. And so that’s the very first thing I do as I am in a unique position because the owner just hired me to fix it. So, therefore, he has to take my advice when I say, “You know what, your website sucks, or your marketing collateral sucks. And by the way, your products don’t work well.” So I then deliver that hard news back to him pretty quickly since the salespeople are not entirely responsible for all of the company’s problems.

Robert Gillette 11:53  

Okay, and that sounds all fine and dandy, but what happens when the number one of the top three things is your salespeople. I mean, so let’s put it this way, I’m a firm believer that every problem is a proportion; it takes two to tango. And it may start at 50/50, but it drifts one direction, even if 90% of the problem aren’t things in my control. So there’s always something within my control. 

Sean O’Shaughnessey 12:18  

Absolutely. There’s a lot within salesperson’s control, 

Robert Gillette 12:21  

Okay, what are the top three things in the salesperson’s control that you see coming up? Time after time, what are the top three? Before you even start, you know one of these three things is happening.

Sean O’Shaughnessey 12:33  

Almost invariably, a salesperson that’s not been successful can’t tell me how his prospect makes money, and more importantly, how his prospect loses money. I don’t know if you’ve ever read the great book Strategic Selling. It was written back in 1981 or 82 or something like that. It was the very first sales book that I read in my career. In chapter eight of Strategic Selling, if I remember correctly, it talks about how you need to create this gap between where the reality is and where your prospect wants to be. And if that gap is not big enough, then you don’t have a deal. So, what I see most of the time, people do not understand 

  • How does your prospect make money?
  • What do they want that outcome to be? 
  • Where do they want that to go? 
  • How do they want that to succeed?

Because they don’t understand those answers, they struggle to put together a proposition for the customer. 

They also spend way too much time talking to a person that doesn’t have a gap. Let’s face it, if there’s no gap between where the prospect wants to be and where they are, don’t even waste your time. Go somewhere else. So that’s the biggest mistake I see salespeople make. They don’t understand why they’re actually talking to that prospect.

Robert Gillette 13:51  

Come on, the prospect has reached out to them, or they’ve taken a cold call of some kind. No executive wastes their time talking to a salesperson for fun. Can’t they just assume that there’s some kind of need, there’s some kind of gap because they’re just in the meeting?

Sean O’Shaughnessey 14:08  

Sure, you can assume that, but I don’t know that that’s true. A lot of people talk about how you need to go after the pain. But the reality is that most corporations are in constant pain. I only do B2B sales, so let’s preface it with that since I know almost nothing about B2C sales. Most corporations are in constant pain. There are lots of things screwed up in a company. So just because the company is in pain doesn’t mean that it’s important for them to spend money to get out of pain. So we really need to understand where they want to be and their goals versus where they are. Just because they’re in pain, they took your call. They are saying, “Yeah, that’s a frustrating thing. Sure, I’ll talk to you about that.” but that doesn’t necessarily mean that they can get funding for that problem. Can they go out and convince their bosses to do it? Can they spend a lot of people’s time trying to figure out how to solve a problem? A great conversation doesn’t mean any of that’s going to happen. 

The one thing that gets funded is the things that management says, “This is a problem.” Management says, “I don’t want to be like this anymore, and I’m willing to spend money on it.” That understanding is why most salespeople might struggle to get that first sale because they just don’t understand that. You are wasting your time working on a problem that a customer is never going to buy. Go work on something else. 

When I talked to you earlier, we talked about my struggle right after 9/11, when the economy went flat. I was a salesperson at the time. And I struggled. I remembered back to my early days and what I learned back when I was in sales training. I realized that to be successful for me, and maybe everyone else is different, to be successful, I had to pick 20 companies and really know everything about what their problems were. If I knew 20 companies and I could describe what they were doing, how they were losing money, how they were making money. In that case, I could actually make a profitable proposition to that customer that actually allowed me to get a deal. I didn’t need to close 20. I needed to close three or four or five in order to make my number because the software that I sold at that time is relatively expensive. So closing six deals in a year was a great thing; closing eight deals was fantastic. And if I was in that situation. I could do that with 20 customers. 

Robert Gillette 16:39  

And I want to make sure we don’t miss something here because I want to spend just a little time diving in. One of the biggest problems I found is that salespeople don’t understand business. So they don’t understand how business is done. I probably need to rebrand the podcast because I’m mostly a B2B guy myself. Businesses don’t spend money solving their second biggest problem. Especially if your big challenge is getting to the decision-maker or power, or whoever really signs the check or really gives the Yes or the No. Often, when you can’t get to that person, it’s because this isn’t that person’s biggest problem. It might be your sales contact’s biggest problem, and it may be their job to solve it. But if you can’t understand that deep emotional pain, as Sandler would say or whatever your sales process tells you, or widening the gap, or whatever vernacular you use that is important. It’s not just about understanding, “Is there an opportunity here?” Rather, “Is this THE opportunity? Is this what they are working on? Is this where resources are going to go?” That’s perfect! Thank you for sharing that. So that’s the first thing you work on, what’s the second thing you work on?

Sean O’Shaughnessey 17:50  

The second thing I work on is their curiosity. 

How curious are you as a person about the world around you, especially the world that your customer lives in? Can you actually talk about how they interact with their customers? Can you actually describe on a whiteboard how your customer or prospect actually goes to market? Can you understand how their supply chain works? Depending on what you’re selling and what’s important to you, how curious are you about them? 

Also, how curious are you about your own product that you sell or your own service? A lot of times, especially in b2b sales, we sell a relatively complicated thing. We need to be very curious about what the product does, how it does it, and how we got there? And what does our competitor do? Be curious about what they do and how do they pitch it. 

So I break that all down and just be curious. Ask questions. Ask really stupid questions if you want to. But just be curious and understand. Write it all down. Make a map in your head or make a map on a piece of paper of all of the things that affect that world. 

Curiosity also breeds success. I think it was Dale Carnegie, so correct me if you think I’m wrong; Dale Carnegie said make somebody else your friend. Are you nice to another person? If you’re friendly to another person, they will be friendly back to you. Unfortunately, that’s not always the case. There are jerks out there, and we all know that. However, in general, if I ask you a lot of questions about your business and how you became successful, that will give you a good impression of me. 

In fact, you kind of said at the beginning of this podcast that I’m on here because I interacted with you. I was curious about your world, and that was just pure curiosity. But it was enough that you said, “Gee, that’s interesting. I’ll talk to Sean.” And that’s exactly what you want to do on a regular basis as a salesperson. Just be curious about everything around you. Don’t explain anything at the beginning; just ask questions. Be curious about how the world works. Be curious about how your world works. And inevitably, you will become smarter, and you will have somebody explain it to you, and there’ll be your friend.

Robert Gillette 20:10  

So I’ve got two things I got to push back about that, because, you know, there are two things that, first of all, the questions that we ask reveal what we’re worried about. So if you’re ever curious about what the prospect is concerned about, listen to the questions they ask and what they revolve around. So if I’m asking questions about a person’s business, especially if I’m in a vertical where I’m supposed to be the expert, doesn’t that make it seem like I don’t know what I’m doing?

Sean O’Shaughnessey 20:37  

Not at all. You should not pretend to be the expert, especially if you are a young salesperson. I’m talking to what I think is your target market, salespeople that have been in their jobs for less than ten years or been in their career for less than ten years. Why in the world would you think that you should be the expert? You need to let them be the expert for you. Let them explain it to you. You’re going to get smarter. You’re going to ask the same question to six people in six different companies in the same vertical. Guess what? You already know the answer. It doesn’t matter; ask them again. What’s different about how you do it. What’s different about how your operation works? What’s different about that? Asking those questions is not so much that you want to get smarter. It’s that you want them to explain it to you. How does it work for them? That reveals what their problems are and what their goals are. It also reveals what they’re willing to fight for in the event that you can actually get the deal done.

Robert Gillette 21:38  

I totally agree! This is the problem. Every sales meeting we walk into, there are actually two meetings. There’s the one you’re having and the one they think they’re having. It is genuinely two different meetings. One of my favorite questions in IT support, I’ll ask people, so tell me, “Do you think cybersecurity is important?” And, of course, everyone says, “Yes.” I’ve never heard a person say, “No.” Wait, one time it happened, and I said, “Oh cool. Hey, this was a great meeting. I’m out.” 

It’s not that I need to be assured that they think it’s important. It’s that I need them to hear them say that it’s important. I can reference it later when I’m asking tougher questions around cybersecurity. Because we need to make sure we’re having the same meeting, I’ll hear the same answer over and over and over, statistically, 100 times a year, in meeting prospects. At a minimum, I need to be sure we’re all on the same page because they didn’t hear the last 99 reps say it, and they’ve maybe never said it out loud. This is about making sure we’re having the same meeting. 

So what’s number three? What’s the number three? I don’t even need to meet you and your sales team. I know this is what you’re doing wrong.

Sean O’Shaughnessey 22:58  

Chances are, the third problem is a little bit of self-doubt. Just a little bit of it. Especially with a younger salesperson that has been potentially struggling a little bit. Maybe he has not made quota, perhaps 70% of quota or 80% of quota, and he has a little bit of self-doubt. So in that respect, they need a cheerleader. 

Your listeners can’t see me; you can. I have a lot of gray hair. I can say, “Look, I’ve done this, and I know, I know your pain, you’re going to be great. You’re going to be fantastic.” There isn’t a single thing that a salesperson has done that I haven’t gone through myself in my career because I’ve been around for so long. They need to know that they are going to be fine. They can fight through. They can be happy, and they should be happy. 

One of the things that I try to teach my salespeople is don’t wait for the big reward. Look for little rewards for yourself to make to get you through the day. I’m really big on focusing on that hard thing that you have to get done. You get a decent size order; give yourself a reward for that. So one of the things I’d like to talk about is a reward if you got a deal that was 10% of your quota or 5% of your quota, depending on how your big your deals are, how big your product is, and what your quota is—all of these factors into this analysis. But whenever you get one of those deals, that’s not enough of a deal that you’re going to make quota or get you to Club at the end of the year, but it is a big deal to you. Maybe 5% of your quota, if that’s the deal that you just closed, especially if you close only close 15 deals in the year. That’s a big thing for you. So, reward yourself for that and be happy about that. Celebrate that. I encourage people to 

  • go out and buy yourself a gift,
  • buy your spouse a gift,
  • do something unique with your spouse,
  • do something unique with your kids.

But only do that thing when you close a 5% of quota deal. 

Have that little goal that you achieve so that you get that 5% deal. “We’re going to go to that special restaurant, and we only go to that restaurant when I close the 5% deal, or 10% deal.” Choose the threshold for whatever makes sense in your world. I coach them on one of those little things that you can reward yourself for doing that will keep you going. Something that you can look forward to. Be rewarded, before the end of the quarter, so that you don’t have to wait for the quarter to end to get that check. You don’t have to wait for the year to happen to stand up on stage; instead, you have a little reward along the way. It will get you through the day because what we need more than anything else is that incremental encouragement that we can do it. If we are successful, you can say, “Gee, that was fun, and I can’t wait to do it again.” 

This technique is especially true if you have a spouse or significant other.

  • You go to that one restaurant,
  • you buy that one gift,
  • you only go to that movie theater for that special evening, 
  • whatever is special to you. 

That way, you are looking forward to that happening again. You have that incremental reward which is more than just the commission check or the paycheck that you received for that deal.

Robert Gillette 26:06  

I have for years and years had the 1% rule. Which is 1% of every commission went to something stupid I would never buy otherwise. A Nerf gun, a drone, a race car, whatever it was. Something that I could never justify reasonably spending money on. But 1% of the commission went to that every time. If I want to save it up, I can. 

But you also touched on something else that I think is really at the core of what I believe is the foundation. So it’s part it’s optical. It’s the foundation about whether or not. Salespeople are successful over a career, and it’s the B-word, it’s belief. It’s not that hard. It is something that is 100% in your control. And quite frankly, no one can actually control it, other than you. You cannot outsource your belief. Other people like a great manager or your own success will feed into it, but belief is something you craft with your own hands at the end of the day, and it is 100% in your control. 

In the last 15-20 seconds or so of this podcast, because we’re running over now, how can someone really build belief without relying on factors such as past success or future dreams when someone’s looking at that where they are today? What can they rely on or deploy to work on belief?.

Sean O’Shaughnessey 27:26  

Yeah, so I’m a big believer in a positive attitude and just saying it to yourself over and over. 

I know this isn’t a Christian podcast, but I’m a Christian. Say a prayer to whatever God you believe in; however that affects you internally, but just ask, “Help me through this process.” 

If you have a significant other in your life, go to that person say, “Hey, every morning, do me a favor, tell me that you think I’m great.” Just push that button a little bit, make it go, because your positive attitude that you can do this means a lot. 

Maybe you do that by doing exercises in the morning. You hit that 20-minute mark or that 40-minute mark on the bike. You made the 4-mile run that morning. Whatever is important to you, but you got to believe. Somehow, deep inside, you have to believe that you can do it. You have to be confident that you can do it. Confidence makes a world of difference, especially when you ask those really stupid questions for the umpteenth time about that person’s business. You know the answer, but you just want to hear him say it one more time. That confidence that you can be there and you can stay in there, and he’s going to treat you like a peer, and that’s important.

Robert Gillette 28:39  

Thank you so much for coming on the show today. I really appreciate your time. I’m going to put your LinkedIn in the show notes if anyone wants to try and hunt you down. 

And then, for those of you who have made it this far into the podcast, we’re looking for two things. Apple podcast reviews are how the algorithm gods can shine on us and introduce the show to other people. Also, I’m launching some really interesting stuff, an ebook that’s coming out, and some in-person events on zoom events that I’m planning. You’re only going to hear about it on the mailing list, so make sure you sign up there as well. 

And thank you again, Sean. 

Sean O’Shaughnessey 29:16  

This has been fun. I enjoyed it. Thank you for having me. 

Robert Gillette 29:19  

Have a great day, everybody. 

Transcribed by and then edited by Sean O’Shaughnessey

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